Skip to main content

Before Angelina Jolie entered a relationship with Billy Bob Thornton, Rosie O’ Donnell would try her luck with the Oscar-winner. But their night out would never come to be after O’ Donnell backed out of seeing Jolie at the last minute.

Angelina Jolie once commented on her sexuality

Angelina Jolie smiling
Angelina Jolie | Alessandra Benedetti – Corbis/Getty Images

During her younger years, Jolie was once very candid about her sexuality. The Tomb Raider star opened up about being able to date both men and a women. To her, gender didn’t determine whether she felt a connection with someone else. Jolie has even revealed she used to be involved in a deep relationship with another woman in the past.

“When I was 20, I fell in love with somebody who happened to be a woman. I was open about it because I wanted people to know that I had been with a woman. I spoke about it because I’d discovered something wonderful and I thought people should know my experience was very real, very,” she once said to Movieline (via The Celeb Post).

Jolie also shared that when she found her female partner at the time, it even caught her off guard.

“I wasn’t looking to have a relationship with a woman. I was surprised when I suddenly found myself having these feelings I always had for men, but for a woman, and wanting to kiss her and wanting to touch her,” she once said according to ABC.

Rosie O’ Donnell once backed out of dating Angelina Jolie because she feared the actor

Talk show host and comic actor Rosie O’ Donnell missed the opportunity to date Jolie. On the Howard Stern Show (via Us Weekly), O’ Donnell revealed that she and Jolie traded phone numbers. But their relationship with each other only went as far as a couple of phone calls.

“We talked on the phone two or three times, but that was that . . .There was a tentative plan to have dinner that never came through,” O’ Donnell said.

This was partially due to O’ Donnell feeling a little intimidated by the star. Still, the View host couldn’t help but think about Jolie years after their phone calls.

“I was a little afraid of her. She’s scary in a sexual kind of way. I have dreams about her a lot still,” O’ Donnell admitted.

Angelina Jolie revealed she had a crush on Michelle Pfeiffer

O’ Donnell wasn’t the only celebrity that caught Jolie’s attention. Over the years, Jolie has dated and even married a couple of high-profile celebrities. The star once even quipped about having a crush on her Maleficent co-star Michelle Pfeiffer during her teenage years. In an interview with Access, Jolie confirmed the crush to the Batman Returns actor herself.

“I definitely was into you when you sang ‘Cool Rider’,” she told Pfeiffer. “You were very hot.”

Jolie also revealed she found Pfeiffer equally attractive in Scarface.

“You were hot then, too,” she added.